79265-36-4

Usage

Uses

Used in Organic Synthesis:
5-Trimethylsilylthiazole is used as a reagent for the formation of carbon-sulfur bonds in organic synthesis. The trimethylsilyl group's protective role for the thiazole ring allows for selective reactions to occur at other functional groups, enhancing the compound's utility in creating complex organic molecules.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 5-Trimethylsilylthiazole is utilized as a precursor in the synthesis of various drugs. Its ability to form carbon-sulfur bonds and protect the thiazole ring during synthesis contributes to the development of new medicinal compounds with potential therapeutic applications.
Used in Agrochemical Production:
5-Trimethylsilylthiazole also finds application in the agrochemical sector, where it is employed as a precursor in the synthesis of agrochemicals. Its role in creating carbon-sulfur bonds is crucial for the development of effective pesticides and other agricultural chemicals.
Used in Specialty Polymers and Materials:
5-TRIMETHYLSILYLTHIAZOLE is used as a precursor in the production of specialty polymers and materials. Its unique structure and reactivity contribute to the creation of advanced materials with specific properties for various high-performance applications.
Used in Chemical Research:
5-Trimethylsilylthiazole is also valuable in chemical research, where it can be employed to explore new reaction pathways, develop novel synthetic methods, and understand the fundamental chemistry of thiazole and related heterocycles.

Upstream product

• 3034-55-7 5-bromo-1,3-thiazole 
• 75-77-4 chloro-trimethyl-silane 
• 288-47-1 1,3-thiazole 
• 79265-34-2 2,5-bis-trimethylsilanyl-thiazole 

Downstream Products

• 112970-07-7 2-Methyl-1-thiazol-5-yl-propan-1-ol 
• 91516-28-8 1-(thiazol-5-yl) ethan-1-one 
• 109776-19-4 Phenyl-thiazol-5-yl-methanol 

Relevant academic research and scientific papers

Efficient access to 5-substituted thiazoles by a novel metallotropic rearrangement

A novel rearrangement process involving the migration of trimethylstannanyl or trimethylsilanyl groups around the thiazole ring provides access to either 2- or 5-metallated thiazoles by tuning the reaction conditions. The proposed mechanism, based on expe

Synthesis of (Trimethylsilyl)thiazoles and Reactions with Carbonyl Compounds. Selectivity Aspects and Synthetic Utility

Synthetic routes to all possible regioisomeric mono- and bis(trimethylsilyl)thiazoles as well as to the tris(trimethylsilyl) derivative via lithiation-silylation sequences of the thiazole ring followed by selective protodesilylation in some cases are described. (Trimethylsilyl)thiazoles serve as thiazolyl donor synthons upon reaction with carbonyl compounds (ketenes, acyl chlorides, aldehydes) for the preparation of mono- and bis-substituted thiazoles in very good yields.Carbodesilylation occurs more readily at the 2- than 5-position, whereas no reaction takes place at the 4-position.A mechanism via a thiazolium 2-ylide as an intermediate is suggested for the carbodesilylation at the 2-position.

NEW PERSPECTIVES IN THIAZOLE CHEMISTRY

Carbon-carbon bond forming reactions at C-2 of the thiazole ring have been carried using two strategies, one involving the addition of organometallic reagents (lithium carbanions of esters, Grignard salts, silyl enol ethers, silyl ketene acetals, silylazoles) to N-acylthiazolium salts; the other involving the addition of carbon electrophiles (ketenes, acyl chlorides, anhydrides, aldehydes) to N-acylthiazolium ylides generated in situ.The reactions have been applied to 1,3-thiazole and 2-trimethylsilyl-1,3-thiazole, the latter being more reactive than the former toward electrophiles.This methodology constitutes a new entry to a variety of functionalized thiazoles and thiazolines which are potential building blocks for the synthesis of natural compounds and analogues of biologically active molecules (penems, arylpropionic acids).Some ring transformations of thiazoles induced by carbon-sulfur bond cleavage are also described.The fundamental role played by the sulfur atom of the thiazole ring in the observed reactions is pointed out and briefly discussed.

Reactions of Trimethylsilylthiazoles with Ketens: A New Route to Regioselective Functionalisation of the Thiazole Ring

2-Trimethylsilylthiazole (2) and 2,5-bis(trimethylsilyl)thiazole (6) undergo ipso-substitution of the 2-SiMe3 group with various ketens affording the thiazolyl-trimethylsiloxy-ethylenes (3) and (7), respectively, which are hydrolysed to the 2-acylthiazoles (4), whereas 5-trimethylsilylthiazole (8) undergoes attack at C-2 by dichloroketen giving the Michael-type adduct 2-dichloroacetyl-5-trimethylsilylthiazole (9c).